data_4B3
# 
_chem_comp.id                                    4B3 
_chem_comp.name                                  "4-BROMO-3-(CARBOXYMETHOXY)-5-{3-[(3,3,5,5-TETRAMETHYLCYCLOHEXYL)AMINO]PHENYL}THIOPHENE-2-CARBOXYLIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C23 H28 Br N O5 S" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-06-26 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        510.441 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     4B3 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        Corina 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        ? 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
# 
loop_
_chem_comp_atom.comp_id 
_chem_comp_atom.atom_id 
_chem_comp_atom.alt_atom_id 
_chem_comp_atom.type_symbol 
_chem_comp_atom.charge 
_chem_comp_atom.pdbx_align 
_chem_comp_atom.pdbx_aromatic_flag 
_chem_comp_atom.pdbx_leaving_atom_flag 
_chem_comp_atom.pdbx_stereo_config 
_chem_comp_atom.model_Cartn_x 
_chem_comp_atom.model_Cartn_y 
_chem_comp_atom.model_Cartn_z 
_chem_comp_atom.pdbx_model_Cartn_x_ideal 
_chem_comp_atom.pdbx_model_Cartn_y_ideal 
_chem_comp_atom.pdbx_model_Cartn_z_ideal 
_chem_comp_atom.pdbx_component_atom_id 
_chem_comp_atom.pdbx_component_comp_id 
_chem_comp_atom.pdbx_ordinal 
4B3 S1   S1   S  0 1 Y N N 44.611 14.046 0.506  -2.593 2.651  -0.181 S1   4B3 1  
4B3 C2   C2   C  0 1 Y N N 44.766 15.439 1.557  -4.012 1.612  -0.207 C2   4B3 2  
4B3 C3   C3   C  0 1 Y N N 45.623 15.180 2.563  -3.654 0.333  0.142  C3   4B3 3  
4B3 C4   C4   C  0 1 Y N N 46.188 13.814 2.526  -2.317 0.172  0.419  C4   4B3 4  
4B3 C5   C5   C  0 1 Y N N 45.732 13.086 1.488  -1.570 1.306  0.303  C5   4B3 5  
4B3 C6   C6   C  0 1 N N N 44.030 16.679 1.225  -5.322 2.030  -0.536 C6   4B3 6  
4B3 O7   O7   O  0 1 N N N 43.577 16.722 0.062  -6.238 1.229  -0.523 O7   4B3 7  
4B3 O8   O8   O  0 1 N N N 43.861 17.602 2.048  -5.557 3.319  -0.864 O8   4B3 8  
4B3 C9   C9   C  0 1 Y N N 46.043 11.652 1.153  -0.115 1.392  0.547  C9   4B3 9  
4B3 C10  C10  C  0 1 Y N N 47.394 11.122 1.218  0.748  0.461  -0.032 C10  4B3 10 
4B3 C11  C11  C  0 1 Y N N 47.634 9.772  0.802  2.112  0.549  0.201  C11  4B3 11 
4B3 C12  C12  C  0 1 Y N N 46.541 8.963  0.280  2.615  1.562  1.009  C12  4B3 12 
4B3 C13  C13  C  0 1 Y N N 45.189 9.448  0.203  1.760  2.484  1.583  C13  4B3 13 
4B3 C14  C14  C  0 1 Y N N 44.977 10.800 0.654  0.402  2.409  1.352  C14  4B3 14 
4B3 BR1  BR1  BR 0 0 N N N 47.415 13.271 3.878  -1.574 -1.492 0.924  BR1  4B3 15 
4B3 O20  O20  O  0 1 N N N 45.915 16.016 3.551  -4.546 -0.688 0.208  O20  4B3 16 
4B3 C21  C21  C  0 1 N N N 47.057 16.832 3.368  -4.751 -1.448 -0.985 C21  4B3 17 
4B3 C22  C22  C  0 1 N N N 47.438 17.445 4.704  -5.767 -2.530 -0.723 C22  4B3 18 
4B3 O25  O25  O  0 1 N N N 46.649 17.400 5.675  -6.120 -3.372 -1.706 O25  4B3 19 
4B3 O26  O26  O  0 1 N N N 48.559 17.981 4.767  -6.265 -2.639 0.373  O26  4B3 20 
4B3 N27  N27  N  0 1 N N N 48.925 9.314  0.962  2.980  -0.382 -0.376 N27  4B3 21 
4B3 C28  C28  C  0 1 N N N 49.292 7.943  1.334  4.425  -0.289 -0.129 C28  4B3 22 
4B3 C30  C30  C  0 1 N N N 50.811 7.752  1.264  5.051  -1.672 -0.307 C30  4B3 23 
4B3 C31  C31  C  0 1 N N N 51.202 6.309  1.655  6.551  -1.613 -0.025 C31  4B3 24 
4B3 C32  C32  C  0 1 N N N 50.516 5.848  2.961  7.239  -0.565 -0.885 C32  4B3 25 
4B3 C33  C33  C  0 1 N N N 49.010 6.159  3.088  6.551  0.789  -0.938 C33  4B3 26 
4B3 C34  C34  C  0 1 N N N 48.728 7.626  2.722  5.045  0.669  -1.144 C34  4B3 27 
4B3 C42  C42  C  0 1 N N N 52.728 6.200  1.871  7.147  -2.990 -0.390 C42  4B3 28 
4B3 C46  C46  C  0 1 N N N 50.826 5.322  0.510  6.806  -1.382 1.463  C46  4B3 29 
4B3 C50  C50  C  0 1 N N N 48.700 5.958  4.579  7.125  1.562  -2.146 C50  4B3 30 
4B3 C54  C54  C  0 1 N N N 48.095 5.209  2.245  6.848  1.617  0.314  C54  4B3 31 
4B3 HO8  HO8  H  0 1 N N N 43.355 18.297 1.645  -6.482 3.509  -1.073 HO8  4B3 32 
4B3 H10  H10  H  0 1 N N N 48.207 11.737 1.575  0.354  -0.325 -0.659 H10  4B3 33 
4B3 H12  H12  H  0 1 N N N 46.754 7.961  -0.062 3.678  1.628  1.189  H12  4B3 34 
4B3 H13  H13  H  0 1 N N N 44.381 8.836  -0.170 2.157  3.268  2.210  H13  4B3 35 
4B3 H14  H14  H  0 1 N N N 43.975 11.201 0.619  -0.262 3.134  1.799  H14  4B3 36 
4B3 H211 1H21 H  0 0 N N N 47.891 16.224 2.988  -5.115 -0.792 -1.776 H211 4B3 37 
4B3 H212 2H21 H  0 0 N N N 46.836 17.627 2.641  -3.809 -1.901 -1.293 H212 4B3 38 
4B3 HO25 HO25 H  0 0 N N N 47.045 17.828 6.425  -6.775 -4.049 -1.490 HO25 4B3 39 
4B3 HN27 HN27 H  0 0 N N N 49.355 9.457  0.071  2.629  -1.089 -0.939 HN27 4B3 40 
4B3 H28  H28  H  0 1 N N N 48.853 7.232  0.618  4.584  0.075  0.882  H28  4B3 41 
4B3 H301 1H30 H  0 0 N N N 51.150 7.949  0.236  4.579  -2.374 0.383  H301 4B3 42 
4B3 H302 2H30 H  0 0 N N N 51.287 8.450  1.968  4.887  -2.015 -1.330 H302 4B3 43 
4B3 H321 1H32 H  0 0 N N N 50.630 4.756  3.022  8.266  -0.425 -0.515 H321 4B3 44 
4B3 H322 2H32 H  0 0 N N N 51.005 6.411  3.769  7.328  -0.955 -1.911 H322 4B3 45 
4B3 H341 1H34 H  0 0 N N N 49.204 8.283  3.465  4.845  0.301  -2.154 H341 4B3 46 
4B3 H342 2H34 H  0 0 N N N 47.641 7.792  2.714  4.584  1.655  -1.037 H342 4B3 47 
4B3 H421 1H42 H  0 0 N N N 53.236 6.174  0.896  6.966  -3.197 -1.445 H421 4B3 48 
4B3 H422 2H42 H  0 0 N N N 53.080 7.070  2.445  8.220  -2.984 -0.200 H422 4B3 49 
4B3 H423 3H42 H  0 0 N N N 52.954 5.278  2.427  6.675  -3.763 0.218  H423 4B3 50 
4B3 H461 1H46 H  0 0 N N N 50.737 5.875  -0.437 6.462  -2.247 2.029  H461 4B3 51 
4B3 H462 2H46 H  0 0 N N N 51.609 4.555  0.415  7.873  -1.238 1.631  H462 4B3 52 
4B3 H463 3H46 H  0 0 N N N 49.866 4.839  0.743  6.264  -0.494 1.791  H463 4B3 53 
4B3 H501 1H50 H  0 0 N N N 49.641 5.910  5.146  6.931  1.003  -3.062 H501 4B3 54 
4B3 H502 2H50 H  0 0 N N N 48.094 6.801  4.944  6.649  2.541  -2.211 H502 4B3 55 
4B3 H503 3H50 H  0 0 N N N 48.142 5.019  4.714  8.200  1.689  -2.019 H503 4B3 56 
4B3 H541 1H54 H  0 0 N N N 47.880 5.674  1.272  7.926  1.675  0.464  H541 4B3 57 
4B3 H542 2H54 H  0 0 N N N 48.610 4.250  2.087  6.444  2.622  0.189  H542 4B3 58 
4B3 H543 3H54 H  0 0 N N N 47.152 5.035  2.784  6.386  1.144  1.180  H543 4B3 59 
# 
loop_
_chem_comp_bond.comp_id 
_chem_comp_bond.atom_id_1 
_chem_comp_bond.atom_id_2 
_chem_comp_bond.value_order 
_chem_comp_bond.pdbx_aromatic_flag 
_chem_comp_bond.pdbx_stereo_config 
_chem_comp_bond.pdbx_ordinal 
4B3 S1  C2   SING Y N 1  
4B3 S1  C5   SING Y N 2  
4B3 C2  C3   DOUB Y N 3  
4B3 C2  C6   SING N N 4  
4B3 C3  C4   SING Y N 5  
4B3 C3  O20  SING N N 6  
4B3 C4  C5   DOUB Y N 7  
4B3 C4  BR1  SING N N 8  
4B3 C5  C9   SING N N 9  
4B3 C6  O7   DOUB N N 10 
4B3 C6  O8   SING N N 11 
4B3 O8  HO8  SING N N 12 
4B3 C9  C10  SING Y N 13 
4B3 C9  C14  DOUB Y N 14 
4B3 C10 C11  DOUB Y N 15 
4B3 C10 H10  SING N N 16 
4B3 C11 C12  SING Y N 17 
4B3 C11 N27  SING N N 18 
4B3 C12 C13  DOUB Y N 19 
4B3 C12 H12  SING N N 20 
4B3 C13 C14  SING Y N 21 
4B3 C13 H13  SING N N 22 
4B3 C14 H14  SING N N 23 
4B3 O20 C21  SING N N 24 
4B3 C21 C22  SING N N 25 
4B3 C21 H211 SING N N 26 
4B3 C21 H212 SING N N 27 
4B3 C22 O25  SING N N 28 
4B3 C22 O26  DOUB N N 29 
4B3 O25 HO25 SING N N 30 
4B3 N27 C28  SING N N 31 
4B3 N27 HN27 SING N N 32 
4B3 C28 C30  SING N N 33 
4B3 C28 C34  SING N N 34 
4B3 C28 H28  SING N N 35 
4B3 C30 C31  SING N N 36 
4B3 C30 H301 SING N N 37 
4B3 C30 H302 SING N N 38 
4B3 C31 C32  SING N N 39 
4B3 C31 C42  SING N N 40 
4B3 C31 C46  SING N N 41 
4B3 C32 C33  SING N N 42 
4B3 C32 H321 SING N N 43 
4B3 C32 H322 SING N N 44 
4B3 C33 C34  SING N N 45 
4B3 C33 C50  SING N N 46 
4B3 C33 C54  SING N N 47 
4B3 C34 H341 SING N N 48 
4B3 C34 H342 SING N N 49 
4B3 C42 H421 SING N N 50 
4B3 C42 H422 SING N N 51 
4B3 C42 H423 SING N N 52 
4B3 C46 H461 SING N N 53 
4B3 C46 H462 SING N N 54 
4B3 C46 H463 SING N N 55 
4B3 C50 H501 SING N N 56 
4B3 C50 H502 SING N N 57 
4B3 C50 H503 SING N N 58 
4B3 C54 H541 SING N N 59 
4B3 C54 H542 SING N N 60 
4B3 C54 H543 SING N N 61 
# 
loop_
_pdbx_chem_comp_descriptor.comp_id 
_pdbx_chem_comp_descriptor.type 
_pdbx_chem_comp_descriptor.program 
_pdbx_chem_comp_descriptor.program_version 
_pdbx_chem_comp_descriptor.descriptor 
4B3 SMILES           ACDLabs              10.04 O=C(O)c3sc(c1cc(ccc1)NC2CC(C)(C)CC(C)(C)C2)c(Br)c3OCC(=O)O                                                                                                               
4B3 InChI            InChI                1.02b InChI=1/C23H28BrNO5S/c1-22(2)9-15(10-23(3,4)12-22)25-14-7-5-6-13(8-14)19-17(24)18(30-11-16(26)27)20(31-19)21(28)29/h5-8,15,25H,9-12H2,1-4H3,(H,26,27)(H,28,29)/f/h26,28H 
4B3 InChIKey         InChI                1.02b OSQARHVGUZHHGT-SKKVRFOWCP                                                                                                                                                
4B3 SMILES_CANONICAL CACTVS               3.341 CC1(C)CC(CC(C)(C)C1)Nc2cccc(c2)c3sc(C(O)=O)c(OCC(O)=O)c3Br                                                                                                               
4B3 SMILES           CACTVS               3.341 CC1(C)CC(CC(C)(C)C1)Nc2cccc(c2)c3sc(C(O)=O)c(OCC(O)=O)c3Br                                                                                                               
4B3 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC1(CC(CC(C1)(C)C)Nc2cccc(c2)c3c(c(c(s3)C(=O)O)OCC(=O)O)Br)C                                                                                                             
4B3 SMILES           "OpenEye OEToolkits" 1.5.0 CC1(CC(CC(C1)(C)C)Nc2cccc(c2)c3c(c(c(s3)C(=O)O)OCC(=O)O)Br)C                                                                                                             
# 
loop_
_pdbx_chem_comp_identifier.comp_id 
_pdbx_chem_comp_identifier.type 
_pdbx_chem_comp_identifier.program 
_pdbx_chem_comp_identifier.program_version 
_pdbx_chem_comp_identifier.identifier 
4B3 "SYSTEMATIC NAME" ACDLabs              10.04 "4-bromo-3-(carboxymethoxy)-5-{3-[(3,3,5,5-tetramethylcyclohexyl)amino]phenyl}thiophene-2-carboxylic acid"   
4B3 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "4-bromo-3-(carboxymethyloxy)-5-[3-[(3,3,5,5-tetramethylcyclohexyl)amino]phenyl]thiophene-2-carboxylic acid" 
# 
